Functional acetic acid derivatives containing phosphorus and herbicidal, growth-regulating agents containing them

ABSTRACT

Compounds of the formula ##STR1## in which R 1  and R 2  denote alkyl, OH, CF 3  or cyanoethyl, A preferably denotes --COOH, R 3  denotes inter alia alkoxycarbonylalkoxy, fairly high-molecular (&gt;C 12 ) alkoxy, alkylcarbonylalkoxy or nitrobenzyloxy, are valuable herbicides and growth regulators.

The phosphonoglycine of the formula (HO)₂ P(O)CH(NH₂))COOH is describedin Japanese Application 54.089,027 as a compound having herbicidalproperties. Numerous derivatives of dimethylphosphinoylhydroxyaceticacid (CH₃)₂ P(O)CH(OH)COOH and related compounds are also disclosed inGerman Offenlegungsschrift 3,238,958.

It has now been found that numerous other functional derivatives,containing phosphorus, of acetic acid possess an excellent herbicidaland growth-regulating action.

The invention therefore relates to compounds of the general formula I##STR2## in which R₁ and R₂ independently of one another denote (C₁-C₄)-alkyl, OH, CF₃ or cyanoethyl,

A denotes the groups --CO--, --CHOH, --CHOR₆, --CHOCONR₇ R₈, --CHNHR₉ or--CHOCOR₁₀,

denotes --XCR₁₁ R₁₂ CXR₁₃, --X(C₁₃ -C₁₈)-alkyl, --X(C₁-C₁₇)-alkylcarbonyl-(C₁ -C₁₇)-alkyl, nitrobenzyloxy, a radical of theformula ##STR3## and, if A=--CHOCOR₁₀, also --OH or --SH; or (C₁-C₁₂)-alkoxy, (C₃ -C₈)-cycloalkoxy, (C₃ -C₆)-alkenyloxy, (C₃-C₆)-alkinyloxy, phenoxy or benzyloxy, it being possible for the groupsmentioned to be substituted in turn by OH, halogen, CF₃, (C₁ -C₄)-alkylor (C₁ -C₄)-alkoxy; or (C₁ -C₆)-alkylthio, (C₃ -C₈)-cycloalkylthio, (C₃-C₆)-alkenylthio, (C₃ -C₆)-alkinylthio, phenylthio or benzylthio, itbeing possible for the groups mentioned to be substituted in turn byhalogen, CF₃, (C₁ -C₄)-alkyl or (C₁ -C₄)-alkoxy; or amino orhydroxylamino; or (C₁ -C₄)-alkylamino, O-(C₁ -C₄)-alkylhydroxylamino,di-(C₁ -C₄)-alkylamino, anilino, phenyl-(C₁ -C₄)-alkylamino,diphenyl-(C₁ -C₄)-alkylamino, N-phenyl-N-(C₁ -C₄)-alkylamino,N-phenyl-N-(C₃ -C₆)-alkenylamino or N-phenyl-N-(C₃ -C₆)-alkinylamino, itbeing possible for the groups mentioned to be substituted in turn by OH,halogen, (C₁ -C₄)-alkyl or (C₁ -C₄)-alkoxy; or hydrazino, β-(C₁-C₄)-alkylhydrazino, β,β-di-(C₁ -C₄)-alkylhydrazino, piperidino,pyrrolidino, morpholino, 2,6-dimethylmorpholino or a radical of theformula ##STR4## R₄ denotes H, OH, SH, halogen, (C₁ -C₄)-alkyl, (C₁-C₄)-alkoxy, allyloxy, propargyloxy, phenoxy, benzyloxy, formyl, CF₃,NO₂, di-(C₁ -C₄)-alkoxymethyl, di-(C₁ -C₄)-alkylthiomethyl or (C₁-C₄)-alkoxycarbonyl,

R₅ denotes H, halogen, (C₁ -C₄)-alkoxy or NO₂,

R₆ denotes (C₁ -C₁₂)-alkyl, benzyl, phenyl, halogenobenzyl,halogenophenyl, allyl, propargyl, CF₃ or tetrahydropyranyl,

R₇ and R₈ independently of one another denote H; or (C₁ -C₁₂)-alkyl, (C₃-C₈)-cycloalkyl, (C₃ -C₆)-alkenyl, (C₃ -C₆)-alkinyl, phenyl, benzyl,benzoyl, phenoxysulfonyl, (C₁ -C₁₂)-alkylsulfonyl, (C₃-C₆)-alkenylsulfonyl or phenylsulfonyl, it being possible for the groupsmentioned to be substituted in turn by halogen, CF₃, CN, (C₁ -C₄)-alkoxyor (C₁ -C₄)-alkoxycarbonyl,

R₉ denotes hydrogen, (C₁ -C₆)-alkyl, (C₃ -C₆)-alkenyl, (C₃ -C₆)-alkinyl,(C₁ -C₄)-acyl, halogen-(C₁ -C₄)-acyl or benzoyl,

R₁₀ denotes (C₁ -C₁₈)-alkyl, (C₃ -C₆)-cycloalkyl, allyl, propargyl,phenyl, benzyl, monohalogenobenzyl, dihalogenobenzyl or aminomethyl,

R₁₁ and R₁₂ independently of one another denote H, (C₁ -C₄)-alkyl, (C₁-C₄)-alkoxy, phenyl or benzyl,

R₁₃ denotes OH or SH; or (C₁ -C₁₈)-alkoxy, (C₃ -C₈)-cycloalkoxy, (C₃-C₁₈)-alkenyloxy, (C₃ -C₆)-alkinyloxy, phenoxy or benzyloxy, it beingpossible for the groups mentioned to be substituted in turn by OH,halogen, CF₃, NO₂, (C₁ -C₄)-alkyl, (C₁ -C₄)-alkoxy or phenoxy; or (C₁-C₄)-alkoxycarbonyl-(C₁ -C₄)-alkoxy, (C₁ -C₄)-alkoxycarbonylbenzyloxy orbenzyloxycarbonylbenzyloxy; or methylthio-(C₁ -C₄)-alkyl,methylsulfinyl-(C₁ -C₄)-alkyl or methylsulfonyl-(C₁ -C₄)-alkyl; or (C₁-C₁₈)-alkylthio, (C₃ -C₈)-cycloalkylthio, (C₃ -C₁₈)-alkenylthio, (C₃-C₆)-alkinylthio, phenylthio or benzylthio, it being possible for thegroups mentioned to be substituted in turn by halogen, CF₃, (C₁-C₄)-alkyl or (C₁ -C₄)-alkoxy; or amino or hydroxylamino; or (C₁-C₁₂)-alkylamino, O-(C₁ -C₄)-alkylhydroxylamino, di-(C₁-C₁₀)-alkylamino, anilino, phenyl-(C₁ -C₄)-alkyl)amino, di[ phenyl-(C₁-C₄)-alkyl]amino, N-phenyl-N-(C₁ -C₄)-alkylamino, N-phenyl-N-(C₃-C₆)-alkenylamino or N-phenyl-N-(C₃ -C₆)-alkinylamino, it being possiblefor the groups mentioned to be substituted in turn by OH, halogen, (C₁-C₄)-alkyl or (C₁ -C₄)-alkoxy; or hydrazino,-(C₁ -C₄)-alkylhydrazino,β,β-di-(C₁ -C₄ -alkylhydrazino, piperidio, pyrrolindino, morpholino,2,6-dimethylmorpholino or a radical of the formula ##STR5## and Xdenotes O or S, and to salts thereof with bases or acids.

In the above, "Hal" or "halogen" preferably denotes chlorine or bromine.If the aliphatic groups mentioned for R₁₃ are substituted, they arepreferably monosubstituted by hydroxyl, (C₁ -C₄)-alkoxy or halogen,especially chlorine. The aromatic groups can be monosubstituted totrisubstituted, preferably by halogen, in particular by chlorine, CF₃,(C₁ -C₂)-alkyl or (C₁ -C₂)-alkoxy.

If one of the radicals R₁, R₂ or R₁₃ denotes --OH or if R₁₃ denotes--SH, the compounds of the formula I are also capable of forming saltswith inorganic and organic bases. Examples of suitable cations of basesare Na⁺, K⁺, NH₄ +, Ca²⁺, Mg²⁺, Zn²⁺, Cu²⁺, Fe⁺², Ni²⁺, (C₁-C₄)-alkyl-NH₃ +, di-(C₁ -C₄)-alkyl-NH₂ +, tri-(C₁ -C₄)-alkyl-NH⁺ or(HOCH₂ CH₂)₃ NH⁺.

Compounds of the general formula I containing in the radicals A and R₃one or more asymmetric carbon atoms or containing an asymmetricphosphorus atom, exist in enantiomeric or diastereomeric forms. Ingeneral, the corresponding compounds according to the invention areobtained in the form of racemates or mixtures of diastereomers. Ifdesired, the customary techniques for the separation of the mixturesinto the sterically, homogeneous constituents can be used. Preparationof the optical isomers in a pure state is also possible by usingsterically homogeneous starting materials.

Compounds in which R₁ and R₂ denote CH₃ or C₂ H₅ ; A denotes CHOH orCHOCOR₁₀ and R₃ denotes OCH₂ COR₁₃, --OCH(CH₃)COR₁₃ or nitrobenzyloxyand R₁₃ has the meanings indicated are preferred.

Particularly preferred compounds are those in which R₁ and R₂ are CH₃, Ais CHOH, R₃ is OCH₂ COR₁₃, OCH(CH₃)COR₁₃ or nitrobenzyloxy and R₁₃ is(C₁ -C₁₈)-alkoxy, allyloxy, propinyloxy, (C₁ -C₄)-halogenoalkoxy, (C₁-C₄)-alkoxycarbonyl-(C₁ -C₄)-alkoxy, benzyloxy, (C₁-C₄)-alkoxycarbonylbenzyloxy, benzyloxycarbonylbenzyloxy, (C₁-C₄)-alkylthio, (C₁ -C₄)-alkylamino, anilino or benzylamino.

Compounds of the formula I in which R₃ is --XCR₁₁ R₁₂ CXR₁₃ are obtainedby reacting compounds of the general formula II ##STR6## withhalogeno(thio)carboxylic acids or esters of the formula III

    HalCR.sub.11 R.sub.12 CXR.sub.13                           III

or hydroxy(thio)carboxylic acid (esters) or mercapto(thio)carboxylicacid (esters) of the formula IV

    HXCR.sub.11 R.sub.12 CXR.sub.13                            IV

Further compounds I in which R₃ is X-alkyl, X-alkylcarbonylalkyl,X-phenylcarbonylalkyl or nitrobenzyloxy are prepared in a manneranalogous to the compounds of German Offenlegungsschrift 3,238,958.

The compounds of the formula I thus obtained can, if appropriate, beconverted into other compounds of the formula I by alkylation,halogenation, benzylation, oxidation, acrylation, amination orhydrogenation. An alkoxy group which may be present in position R₁₃ canbe saponified, or acids can be converted into their salts.

The reactions can be carried out with or without the addition ofsolvents at temperatures of 20°-100° C.; suitable solvents are, ifappropriate, inert solvents, such as dioxane, tetrahydrofuran,acetonitrile, dimethoxyethane, methylene dichloride, toluene ordimethylformamide.

In some cases it is suitable to accelerate the reaction by adding bases.Suitable bases are alkali metal hydroxides or alcoholates, such as NaOH,KOH, NaOCH₃ or K tert.-butylate, or tertiary nitrogen bases, such astriethylamine or methyldiisopropylamine; and also fluorides, such as KF,CsF, or NaF.

The starting materials of the formulae II and V are obtained, forexample, by the process indicated in German Offenlegungsschrift3,238,958. The starting materials of the formulae III, IV and VI areknown from the literature or can be prepared by processes known from theliterature.

The compounds according to the invention possess an excellent and verybroad herbicidal action against a broad spectrum of annual and perennialgrass-like weeds and weeds on road verges, in industrial plants or inrailroad installations. The invention also relates, therefore, toherbicidal agents containing the compounds of the formula I and to theuse thereof for combating undesired plant growth.

The active compounds are suitable both for use in agriculture and forcombating weeds. Use in annual or perennial agricultural crops ispossible provided that the nature of the application and/or the age ofthe crop plant ensures that the crop plants or their sensitive greenparts do not suffer damage. Examples of possible use of this type areplantations, tree nurseries, vineyards, etc.

Since using the new compounds in crops of useful plants before theemergence of the crop plants causes only slight damage or none at all,they can still be used against weeds before the emergence of the seed orbefore sowing or after the harvest.

However, the compounds according to the invention can also be employedeven against plant growth of the useful plant (for example cotton orpotatoes) which interferes in harvesting.

Depending on the dosage used, typical growth-regulating effects can alsobe achieved by means of the new compounds; thus, for example, it ispossible to influence the growth of the plants, but also the content ofdesired plant constituents. The compounds are thereby suitable as growthregulators in crops of useful plants, such as, for example, cereals,maize, sugar cane, tobacco, rice and sorghum. On the other hand, it isalso possible to regulate crops of plants, for instance cultivatedlawns, or plant communities on the verges of paths and roads and alsoornamental plants.

The effect of using the compounds according to the invention is toinhibit vegetative growth in a large number of monocotyledonous anddicotyledonous plants and, as a consequence thereof, to increase, interalia, the carbohydrate content in the plants or in the fruit thereof.The consequence of this is in many cases an advantageous effect on thecontent of desired plant constituents, such as proteins or carbohydrates(starch or sugar).

For example, there is an increase in the sucrose content in the case ofsugar cane and sugar beet, and of the levulose content in the case offruit and grapes; in the case of other plants, such as potatoes, maize,millet (sorghum) and green fodder (clover and lucerne) there is anincrease in the starch content. The advantages achieved thereby aremanifest and require no explanation.

Application is effected about one week to 5 months before the harvest.After the expiration of this time the degree of ripeness, and hence alsothe carbohydrate content, caused by the active compounds has reached amaximum. In general it should be borne in mind that the rate of growthand vegetative period in the crops can vary within considerable limits.Sugar cane, for example, requires 1-3 years until it is ripe forharvesting, depending on its habitat and the climate. Similarly, thetime of application must also be varied. In the case of sugar cane thiscan be, for example, 1 to 13 weeks before harvest.

The agents can be applied in the customary formulations as wettablepowders, emulsifiable concentrates, atomizable solutions, dustingagents, dressing agents, dispersions, granules or microgranules.

Wettable powders are preparations which are uniformly dispersible inwater and which, in addition to the active compound and apart, ifappropriate, from a diluent or inert material, also contain wettingagents, for example polyoxethylated fatty alcohols, alkylsulfonates oralkylphenylsulfonates, and dispersing agents, for example sodiumligninsulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodiumdibutylnaphthalenesulfonate or sodium oleoylmethyltauride. Preparationis effected in a customary manner, for example by grinding and mixingthe components.

Emulsifiable concentrates can be prepared, for example, by dissolvingthe active compound in an inert organic solvent, for example butanol,cyclohexanone, dimethylformamide, xylene or fairly high-boiling aromaticcompounds or hydrocarbons with the addition of one or more emulsifiers.In the case of liquid active compounds it is also possible to dispense,wholly or partly, with the solvent component. The following are examplesof emulsifiers which can be used: calcium alkylarylsulfonates, such asCa dodecylbenzenesulfonate, or nonionic emulsifiers, such as fatty acidpolyglycol esters, alkylarylpolyglycol ethers, fatty alcohol polyglycolethers, propylene oxide/ethylene oxide condensation products, fattyalcohol propylene oxide/ethylene oxide condensation products, alkylpolyglycol ethers, sorbitan fatty acid esters, polyoxethylenesorbitanfatty acid esters or polyoxethylenesorbitol esters.

Dusting agents can be obtained by grinding the active compound withfinely divided solid materials, for example talc, natural clays, such askaolin, bentonite or pyrophillite, or diatomaceous earth.

Granules can be prepared either by atomizing the active compound ontoadsorptive, granulated inert material or by applying concentrations ofactive compound to the surface of carriers, such as sand, kaolinite orgranulated inert material, by means of binders, for example polyvinylalcohol, sodium polyacrylate or mineral oils. It is also possible togranulate suitable active compounds, if desired as a mixture withfertilizers, in the manner customary for the production of fertilizergranules.

In wettable powders the concentration of active compound is, forexample, about 10 to 90% by weight; the remainder up to 100% by weightis composed of customary formulation ingredients. In the case ofemulsifiable concentrates, the concentration of active compound can beabout 10 to 80% by weight. Formulations in the form of dusts contain inmost cases 5 to 20% by weight of active compound, while atomizablesolutions contain about 2 to 20% by weight. In the case of granules, thecontent of active compound depends in part on whether the activecompound is present as a liquid or solid and on the granulationauxiliaries, fillers and the like which are used.

In addition, the active compound formulations mentioned contain, ifappropriate, the tackifiers, wetting agents, dispersing agents,emulsifiers, penetration agents, solvents, fillers or carriers which arecustomary in the particular case.

For application, the concentrates, present in a commercially customaryform, are, if appropriate, diluted in a customary manner, for examplewith water in the case of wettable powders, emulsifiable concentratesand dispersions and, in part, also in the case of microgranules.Formulations in the form of dusts and granules and also atomizablesolutions are usually not diluted further with other inert materialsbefore application.

Mixtures or mixed formulations with other active compounds, such as, forexample, insecticides, acaricides, herbicides, fertilizers, growthregulators or fungicides, are possible in a given case. Particularly inthe case of mixtures with fungicides, synergistic increases ineffectiveness can also be achieved in some cases.

The concentrations for application can vary within wide limits,depending on the purpose of use and the time of application. For use asherbicides, concentrations between 0.3 and 10, preferably 0.5 to 3,kg/hectare are suitable. When used as growth regulators, theconcentrations for application are naturally lower and are approx. 0.1-2kg/hectare, it being possible for the required concentration to varyconsiderably depending on the species of plant.

The invention is illustrated by the following examples.

EXAMPLE 1 Phenacyl 2-dimethylphosphinoyl-2-hydroxyacetate

6.38 g (0.1 mol) of potassium fluoride, 9.95 g (0.06 mol) ofλ-bromoacetophenone and 7.6 g (0.05 mol) of2-dimethylphosphinoyl-2-hydroxyacetic acid are dissolved in 250 ml ofdimethylformamide, and the mixture is stirred for 4 hours at 65° C.; DMFis removed by distillation and the residue is stirred with CH₂ Cl₂ tocomplete the reaction. Yield 8.5 g (63%), melting point 147° C.

The following compounds are obtained analogously:

                                      TABLE 1                                     __________________________________________________________________________     ##STR7##                                                                     Example                                                                       No.  R.sub.1   R.sub.2                                                                            A             R.sub.3                M.p.                 __________________________________________________________________________                                                             [°C.]         2    CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 C.sub.6 H.sub.4 NO.sub.2                                                                   121                  3    CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 C.sub.6 H.sub.4 NO.sub.2 (o)      4    CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 C.sub.6 H.sub.4 NO.sub.2 (m)      5    CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COC.sub.6 H.sub.4 Br(p)                                                                    163                  6    CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COC.sub.6 H.sub.4 Br(o)           7    CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COC.sub.6 H.sub.4 Br(m)           8    CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COOH         Oil                  9    CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.3   115                  10   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOC.sub.2 H.sub.5                                                                          107                  11   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOC.sub.3 H.sub.7 (n)                                                                       82                  12   CH.sub.3  CH.sub. 3                                                                          CHOH          OCH.sub.2COOC.sub.6 H.sub.13 (n)                                                                      65-7                13   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOC.sub.7 H.sub.15 (n)                                                                      72                  14   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOC.sub.10 H.sub.21 (n)                                                                     76-8                15   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOC.sub.12 H.sub.25 (n)                                                                     88-90               16   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOC.sub.18 H.sub.37 (n)                                                                     98-100              17   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOC.sub.18 H.sub.35 (n)                                                                    Oil                                                    (Oleyl)                                     18   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2CH(CH.sub.3)C.sub.2                                       H.sub.5                Oil                  19   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOC.sub.4 H.sub.9 (tert.)                                                                  118                  20   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCyclohexyl Oil                  21   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOC.sub.6 H.sub.10 CH.sub.3                                         (o)                    130-4                22   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCyclopropyl                                                                              Oil                  23   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 CCH                                                                             Oil                  24   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 CH.sub.2 Br                                                                     Oil                  25   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COOCH.sub.2 CH.sub.2 CH.sub.2                                       Br                     Oil                  26   CH.sub.3  CH.sub.3                                                                           CHOH                                                                                         ##STR8##              Oil                  27   CH.sub.3  CH.sub.3                                                                           CHOH                                                                                         ##STR9##              Oil                  28   CH.sub.3  CH.sub.3                                                                           CHOH                                                                                         ##STR10##             Oil                  29   CH.sub.3  CH.sub.3                                                                           CHOH                                                                                         ##STR11##             Oil                  30   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 C.sub.6 H.sub.5                                                                  95                  31   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 C.sub.6 H.sub.4                                          CF.sub.3 (p)                                32   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 C.sub.6 H.sub.4                                          CF.sub.3 (o)                                33   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 C.sub.6 H.sub.4                                          CF.sub.4 (m)                                34   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 C.sub.6 H.sub.4                                          NO.sub.2 (p)           147                  35   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 C.sub.6 H.sub.4                                          NO.sub.2 (o)                                36   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 C.sub.6 H.sub.4                                          NO.sub.2 (m)                                37   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 C.sub.6 H.sub.3                                          Cl.sub.2 (o, p)        Oil                  38   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 C.sub.6 H.sub.4                                          OC.sub.6 H.sub.5 (m)   133                  39   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COSC.sub.2 H.sub.5                                                                          83-6                40   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COSC.sub.4 H.sub.9 (n)            41   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COSC.sub.10 H.sub.21 (n)          42   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COSCH.sub.2 CHCH.sub.2            43   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COSCH.sub.2 C.sub.6 H.sub.5                                                                Oil                  44   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COSC.sub.6 H.sub.5                                                                         Oil                  45   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 CONH.sub.2                        46   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 CONHC.sub.2 H.sub.5               47   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 CONHCH.sub.2 C.sub.6 H.sub.5                                                               Oil                  48   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 CONHC.sub.6 H.sub.5                                                                        Oil                  49   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 CONHC.sub.8 H.sub.17 (n)          50   CH.sub.3  CH.sub.3                                                                            ##STR12##    CH.sub.3                93-5                51   CH.sub.3  CH.sub.3                                                                            ##STR13##    CH.sub.3               Oil                  52   CH.sub.3  CH.sub.3                                                                            ##STR14##    CH.sub.3               Oil                  53   CH.sub.3  CH.sub.3                                                                            ##STR15##    CH.sub.3                                    54   CH.sub.3  CH.sub.3                                                                            ##STR16##    CH.sub.2 C.sub.6 H.sub.5                    55   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COSC.sub.6 H.sub.13 (n)                                                                     Oil                  56   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COSC.sub.12 H.sub.25 (n)                                                                     69-71               57   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2CON(C.sub.2 H.sub.5).sub.2                                                                  104-6                58   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2CON(C.sub.8 H.sub.17).sub.2                                          (n)                    Oil                  59   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2CONHC.sub.6 H.sub.3 Cl.sub.2                                         (o, o)                 198                  60   CH.sub.3  CH.sub.3                                                                           CHOH          OC.sub.2 H.sub.4 COC.sub.2 H.sub.5          61   CF.sub.3  CH.sub.3                                                                           CHOH          OC.sub.2 H.sub.4 COC.sub.2 H.sub.5          62   C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CHOH          OC.sub.2 H.sub.4 COC.sub.2 H.sub.5          63   CH.sub.3  CH.sub.3                                                                           CHOH          OC.sub.2 H.sub.4 COC.sub.4 H.sub.9 (n)      64   C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CHOH          OCH.sub.2 CONH.sub.2                        65   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 CONH.sub.2                        66   CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OCH.sub.2 CONHC.sub.4 H.sub.9 (n)           67   CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OCH.sub.2 CONHC.sub.4 H.sub.9 (n)           68   CH.sub.3  CH.sub.3                                                                           CHOCOCH.sub.2 C.sub.6 H.sub.5                                                               OCH.sub.2 CONHOH                            69   CH.sub.3  CH.sub.3                                                                           CHOCOCH.sub.2 C.sub.6 H.sub.5                                                               OCH.sub.2 CONHOH                            70   CH.sub.3  CH.sub.3                                                                           CHOCOCH.sub.2 C.sub.6 H.sub.5                                                               OCH.sub.2 CONHNH.sub.2                      71   CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 CONHNH.sub.2                      72   CH.sub.3  CH.sub.3                                                                           CHOH                                                                                         ##STR17##                                  73   CH.sub.3  CH.sub.3                                                                           CHOH                                                                                         ##STR18##                                  74   CH.sub.3  CH.sub.3                                                                           CHNH.sub.2    OCH.sub.2 HCOOC.sub.2 H.sub.5               75   CH.sub.3  CH.sub.3                                                                           CHNHC.sub.2 H.sub.5                                                                         OCH.sub.2 HCOOC.sub.2 H.sub.5               76   CH.sub.3  CH.sub.3                                                                           CHNHC.sub.2 H.sub.5                                                                         OCH.sub.2 COOCH.sub.3                       77   CH.sub.3  CH.sub.3                                                                           CHNHC.sub.2 H.sub.5                                                                         OCH.sub.2 COOCH.sub.2 C.sub.6 H.sub.5       78   CH.sub.3  CH.sub.3                                                                           CHOCH.sub.3   OCH.sub.2 COOCH.sub.3                       79   C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CHOCH.sub.3   OCH.sub.2 COOCH.sub.3                       80   C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CHOCH.sub.3   OCH.sub.2 COOCH.sub.3                       81   C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CHOC.sub.2 H.sub.5                                                                          OCH.sub.2 COOCH.sub.3                       82   C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CHOC.sub.2 H.sub.5                                                                          OCH.sub.2 COOCH.sub.3                       83   C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CHOCH.sub.2 C.sub.6 H.sub.5                                                                 OCH.sub.2 COOCH.sub.3                       84   CF.sub.3  CH.sub.3                                                                           CHOCH.sub.2 C.sub.6 H.sub.5                                                                 OCH.sub.2 COOCH.sub.3                       85   CH.sub.3  CH.sub.3                                                                           CHOC.sub.6 H.sub.4 Cl(o)                                                                    OCH.sub.2 COOCH.sub.3                       86   CH.sub.3  CH.sub.3                                                                           CHOC.sub.6 H.sub.4 Cl(o)                                                                    OCH.sub.2 COOCH.sub.3                       87   CH.sub.3  CH.sub.3                                                                           CHOCON(CH.sub.3).sub.2                                                                      OCH(CH.sub.3)COOCH.sub.3                    88   C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CHOCON(CH.sub.3).sub.2                                                                      OCH(CH.sub.3)COOCH.sub.3                    89   C.sub.4 H.sub.9 (n)                                                                     CH.sub.3                                                                           CHOCON(CH.sub.3).sub.2                                                                      OCH(CH.sub.3)COOCH.sub.3                    90   CF.sub.3  CH.sub.3                                                                           CHOCON(CH.sub.3).sub.2                                                                      OCH(CH.sub.3)COOCH.sub.3                    91   OH        CH.sub.3                                                                           CHOCON(CH.sub.3).sub.2                                                                      OCH(CH.sub.3)COOCH.sub.3                    92   CH.sub.3  CH.sub.3                                                                           CHOCONHC.sub.6 H.sub.5                                                                      OCH(CH.sub.3)COOC.sub.2 H.sub.5             93   C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CHOCONHC.sub.6 H.sub.5                                                                      OCH(CH.sub.3)COOC.sub.2 H.sub.5             94   C.sub.4 H.sub.9 (n)                                                                     CH.sub.3                                                                           CHOCONHC.sub.6 H.sub.5                                                                      OCH(CH.sub.3)COOC.sub.2 H.sub.5             95   CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OC(CH.sub.3).sub.2 COOCH.sub.3              96   CF.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OCH(CH.sub.3)COOC.sub.2 H.sub.5             97   OH        CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OCH(CH.sub.3)COOC.sub.2 H.sub.5             98   C.sub.4 H.sub.9 (n)                                                                     C.sub.4 H.sub.9 (n)                                                                CHOCOC.sub.6 H.sub.5                                                                        OCH(CH.sub.3)COOC.sub.2 H.sub.5             99   CH.sub.3  CH.sub.3                                                                           CHOCOCH.sub.2 CHCH.sub.2                                                                    OCH.sub.2COOC.sub.2 H.sub.5                 100  CF.sub.3  CH.sub.3                                                                           CHOCOCH.sub.2 CHCH.sub.2                                                                    SCH.sub.2COOCH.sub.3                        101  C.sub.4 H.sub.9 (n)                                                                     C.sub.4 H.sub.9 (n)                                                                CHOCOCH.sub.2 CHCH.sub.2                                                                    SCH.sub.2COOCH.sub.3                        102  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CHOCOCH.sub.2 CHCH.sub.2                                                                    SCH.sub.2COOCH.sub.3                        103  CH.sub.2CH.sub.2CN                                                                      CH.sub.3                                                                           CHOCON(CH.sub.3).sub.2                                                                      OCH(CH.sub.3 )COOCH.sub.3                   104  CH.sub.2CH.sub.2CN                                                                      CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OCH(CH.sub.3)COOC.sub.2 H.sub.5             105  CH.sub.2CH.sub.2CN                                                                      CH.sub.3                                                                           CHOCOCH.sub.2CHCH.sub.2                                                                     OCH(CH.sub.3)COOC.sub.4 H.sub.9 (n)         106  CH.sub.2CH.sub.2CN                                                                      CH.sub.3                                                                           CHOCONHC.sub.6 H.sub.5                                                                      OCH(CH.sub.3)COOC.sub.2 H.sub.5             107  CH.sub.2CH.sub.2CN                                                                      CH.sub.3                                                                           CHOCONHC.sub.6 H.sub.5                                                                      OCH(CH.sub.3)COOC.sub.6 H.sub.4                                               NO.sub.2 (m)                                108  C.sub.2 H.sub.5                                                                         CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OCH(CH.sub.3)COOC.sub.6 H.sub.4                                               NO.sub.2 (m)                                109  CF.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OCH(CH.sub.3)COOC.sub.6 H.sub.4                                               NO.sub.2 (m)                                110  C.sub.4 H.sub.9 (n)                                                                     CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OCH(CH.sub.3)COOC.sub.6 H.sub.4                                               NO.sub.2 (m)                                111  CH.sub.3  CH.sub.3                                                                           CHOCON(CH.sub.3).sub.2                                                                      OCH(CH.sub.3)COOC.sub.6 H.sub.4                                               NO.sub.2 (m)                                112  C.sub.3 H.sub.7 (i)                                                                     CH.sub.3                                                                           CHOCON(CH.sub.3).sub.2                                                                      OCH(CH.sub.3)COOC.sub.6 H.sub.4                                               NO.sub.2 (m)                                113  C.sub.3 H.sub.7 (i)                                                                     C.sub.3 H.sub.7 (i)                                                                CHOCON(CH.sub.3).sub.2                                                                      OCH(CH.sub.3)COOC.sub.6 H.sub.4                                               NO.sub.2 (m)                                114  CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OH                                          115  CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        SH                                          116  CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OCH.sub.3                                   117  CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OC.sub.2 H.sub.5                            118  CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OCH.sub.2C.sub.6 H.sub.5                    119  CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        SCH.sub.2C.sub.6 H.sub.5                    120  CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OC.sub.6 H.sub.4 OC.sub.6 H.sub.5 (p)       121  CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        OC.sub.6 H.sub.4 OC.sub.6 H.sub.5 (m)       122  CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        N(C.sub.2 H.sub.5).sub.2                    123  CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        NH.sub.2                                    124  CH.sub.3  CH.sub.3                                                                           CHOCOC.sub.6 H.sub.5                                                                        NHC.sub.2 H.sub.5                           125  CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COOCH.sub.2 COOC.sub.2                                              H.sub.5                                     126  CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COOC.sub.2 H.sub.4COOCH.sub.3     127  CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2COOCH.sub.2 C.sub.6 H.sub.4COOC                                      H.sub.2 C.sub.6 H.sub. 5 (p)                128  CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COOCH.sub.2 C.sub.6 H.sub.4                                         COOC.sub.2 H.sub.5 (p)                      129  CH.sub.3  CH.sub.3                                                                           CHOH          OCH.sub.2 COOCH.sub.2COOC.sub.4 H.sub.9                                       (n)                                         __________________________________________________________________________

(B) Formulation Examples

(a) A dusting agent is obtained by mixing 10 parts by weight of activecompound and 90 parts by weight of talc or an inert substance andcomminuting the mixture in a hammer mill.

(b) A wettable powder which is readily dispersible in water is obtainedby mixing 25 parts by weight of active compound, 64 parts by weight ofkaolin-containing quartz as an inert substance, 10 parts by weight ofpotassium ligninsulfonate and 1 part by weight of sodiumoleoylmethyltauride as a wetting and dispersing agent, and grinding themixture in a pinned disk mill.

(c) A dispersion concentrate which is readily dispersible in water isobtained by mixing 20 parts by weight of active compound with 6 parts byweight of an alkylphenol polyglycol ether (Triton X 207), 3 parts byweight of isotridecanol polyglycol ether (8 EO) and 71 parts by weightof paraffinic mineral oil (boiling range, for example, approx. 255° toover 377° C.), and grinding the mixture in a ball mill to a fineness ofless than 5 microns.

(d) An emulsifiable concentrate is obtained from 15 parts by weight ofactive compound, 75 parts by weight of cyclohexanone as solvent and 10parts by weight of oxethylated nonylphenol (10 EO) as emulsifier.

(c) Biological Examples EXAMPLE 1

Seeds or pieces of rhizome of grass-like weeds and weeds were sown insandy loam soil in plastic pots (φ 9 cm) and were cultivated in agreenhouse under good growth conditions for 3-5 weeks. The compoundsaccording to the invention, formulated as wettable powders or aqueoussolutions, were then sprayed onto the parts of the plants above groundin the form of aqueous suspensions or atomizable solutions,respectively. The amount of water used corresponded to 600-800liters/hectare.

After approx. 3 weeks waiting time in a greenhouse under optimalconditions for growth, the herbicidal action was assessed visually.

The results of the tests with the new compounds according to theinvention are assembled in Table 2. The following code was used in thesetests:

0=no action

1=0-20% action

2=20-40% action

3=40-60% action

4=60-80% action

5=80-100% action

The figures shown in Table 2 afford clear proof of the very goodherbicidal effectiveness of the new compounds against a broad spectrumof economically important weeds.

Abbreviations used in Table 2

SIA=Sinapis arvensis

CRS=Crysanthemum segctum

ECG=Echinochloa crus galli

LOM=Lolium multiflorum

a.i.=active ingredient

                  TABLE 2                                                         ______________________________________                                        Herbicidal effect of the compounds, according                                 to the invention, used in the post-emergence technique                               Dosage                                                                 Example                                                                              kg of a.i./ Herbicidal effect                                          No.    hectare     SIA    CRS    ECG   LOM                                    ______________________________________                                         2     2.5         5      5      4     5                                       1     2.5         5      5      4     5                                       5     2.5         5      4      5     5                                       8     2.5         5      5      5     5                                       9     2.5         5      4      5     5                                      10     2.5         5      4      4     5                                      11     2.5         5      5      5     5                                      12     2.5         5      5      5     5                                      14     2.5         5      5      5     5                                      15     2.5         5      3      3     4                                      16     2.5         5      4      4     5                                      17     2.5         5      3      2     4                                      18     2.5         5      5      5     5                                      19     2.5         5      5      4     5                                      20     2.5         4      1      1     1                                      21     2.5         5      4      4     5                                      22     2.5         3      1      1     1                                      23     2.5         5      5      4     5                                      24     2.5         5      4      4     5                                      25     2.5         5      4      5     5                                      26     2.5         4      1      1     1                                      27     2.5         5      5      5     5                                      28     2.5         5      4      4     5                                      29     2.5         5      4      3     3                                      30     2.5         5      5      5     5                                      31     2.5         4      4      4     5                                      34     2.5         5      4      2     3                                      37     2.5         5      1      1     1                                      38     2.5         5      3      2     2                                      39     2.5         5      4      5     5                                      43     2.5         4      4      4     4                                      47     2.5         5      5      5     5                                      48     2.5         5      4      4     5                                      55     2.5         5      5      5     5                                      56     2.5         2      1      1     1                                      57     2.5         4      5      5     5                                      58     2.5         5      4      4     3                                      59     2.5         5      5      5     5                                      ______________________________________                                    

We claim:
 1. A compound of formula I ##STR19## in which R₁ and R₂ may bethe same or different and each is (C₁ -C₄)-alkyl, CF₃ or cyanoethyl;A is--CHOH--, --CHOR₆, --CHOCONR₇ R₈ or --CHOCOR₁₀ ; R₃ is --XCR₁₁ R₁₂CXR₁₃, --X(C₁ -C₁₇)-alkylcarbonyl-(C₁ -C₁₇)-alkyl, nitrobenzyloxy or aradical of the formula ##STR20## R₄ is H, OH, SH, halogen, (C₁-C₄)-alkyl, (C₁ -C₄)-alkoxy, allyloxy, propargyloxy, phenoxy, benzyloxy,formyl, CF₃, NO₂, di-(C₁ -C₄)-alkoxymethyl, di-(C₁ -C₄)-alkylthiomethylor (C₁ -C₄)-alkoxycarbonyl; R₅ is H, halogen, (C₁ -C₄)-alkoxy or NO₂, R₆denotes (C₁ -C₁₂)-alkyl, benzyl, phenyl, halogenobenzyl, halogenophenyl,allyl, propargyl, CF₃ or tetrahydropyranyl, R₇ and R₈ may be the same ordifferent and each is H, (C₁ -C₁₂)-alkyl, (C₃ -C₈)-cycloalkyl, (C₃-C₆)-alkenyl, (C₃ -C₆)-alkinyl, phenyl, benzyl, benzoyl,phenoxysulfonyl, (C₁ -C₁₂)-alkylsulfonyl, (C₃ -C₆)-alkenylsulfonyl orphenylsulfonyl, it being possible for the groups mentioned to besubstituted in turn by halogen, CF₃, CN, (C₁ -C₄)-alkoxy or (C₁-C₄)-alkoxycarbonyl; R₁₀ is (C₁ -C₁₈)-alkyl, (C₃ -C₆)-cycloalkyl, allyl,propargyl, phenyl, benzyl, monohalogenobenzyl, dihalogenobenzyl oraminomethyl; R₁₁ and R₁₂ may be the same or different and each is H, (C₁-C₄)-alkyl, (C₁ -C₄)-alkoxy, phenyl or benzyl; R₁₃ is: OH or SH; (C₁-C₁₈)-alkoxy, (C₃ -C₈)-cycloalkoxy, (C₃ -C₁₈)-alkenyloxy, (C₃-C₆)-alkinyloxy, phenoxy or benzyloxy, it being possible for the groupsmentioned to be substituted in turn by OH, halogen, CF₃, NO₂, (C₁-C₄)-alkyl, (C₁ -C₄)-alkoxy or phenoxy; (C₁ -C₄)-alkoxycarbonyl-(C₁-C₄)-alkoxy, (C₁ -C₄)-alkoxycarbonylbenzyloxy orbenzyloxycarbonylbenzyloxy; methylthio-(C₁ -C₄)-alkyl,methylsulfinyl-(C₁ -C₄)-alkyl or methylsulfonyl-(C₁ -C₄)-alkyl; (C₁-C₁₈)-alkylthio, (C₃ -C₈)-cycloalkylthio, (C₃ -C₁₈)-alkenylthio, (C₃-C₆)-alkinylthio, phenylthio or benzylthio, it being possible for thegroups mentioned to be substituted in turn by halogen, CF₃, (C₁-C₄)-alkyl or (C₁ -C₄)-alkoxy; amino or hydroxylamino; (C₁-C₄)-alkylamino, O-(C₁ -C₄)-alkylhydroxylamino, di-(C₁ -C₁₀)-alkylamino,anilino, phenyl-(C₁ -C₄)-alkyl)amino, di[phenyl-(C₁ -C₄)-alkyl] amino,N-phenyl-N-(C₁ -C₄)-alkylamino, N-phenyl-N-(C₃ -C₆)-alkenylamino orN-phenyl-N-(C₃ -C₆)-alkinylamino, it being possible for the groupsmentioned to be substituted in turn by OH, halogen, (C₁ -C₄)-alkyl or(C₁ -C₄)-alkoxy; or hydrazino, β-(C₁ -C₄)-alkylhydrazino, β,β-di-(C₁-C₄)-alkylhydrazino, piperidino, pyrrolidino, morpholino,2,6-dimethylmorpholino or a radical of the formula ##STR21## and X is Oor S; and salts thereof with bases or acids.
 2. A compound as claimed inclaim 1, in which R₁ and R₂ are CH₃ or C₂ H₅, A is CHOH, R₃ is --OCH₂COR₁₃ or nitrobenzyloxy and R₁₃ has the meanings indicated in claim 1.3. A compound as claimed in claim 2, in which R₁ and R₂ are methyl, A isCHOH and R₁₃ is (C₁ -C₁₈)-alkoxy, allyloxy, propinyloxy, (C₁-C₄)-halogenoalkoxy, (C₁ -C₄)-alkoxycarbonyl-(C₁ -C₄)-alkoxy, benzyloxy,(C₁ -C₄)-alkoxycarbonylbenzyloxy, benzyloxycarbonylbenzyloxy, (C₁-C₄)-alkylthio, (C₁ -C₄)-alkylamino, anilino or benzylamino.
 4. Thecompound of claim 3 in which R₁ and R₂ are methyl, A is CHOH and R₃ is--OCH₂ --COOCH₃.
 5. A herbicidal and growth-regulating agent whichcomprises an effective amount of a compound as claimed in claim 1 and aninert carrier.
 6. A process for combating undesired plant growth, whichcomprises applying an effective amount of a compound as claimed in claim1 to the plants or to the areas to be treated.
 7. A process forregulating the growth of useful plants, which comprises applying aneffective amount of a compound as claimed in claim 1 to the plants.